Fluorescent H-Aggregate Vesicles and Tubes of a Cyanine Dye and Their Potential as Light-Harvesting Antennae.

H-aggregates of π-conjugated dyes are an ordered supramolecular structure. However, the non-fluorescence behavior of H-aggregates greatly limits their potential applications. In this paper, we report the formation of fluorescent H-aggregates with vesicular and tubular morphologies by the self-assembly of 3,3'-diethylthiacarbocyanine iodide (DiSC2(3)) in ammonia/methanol mixtures. The transition from H-aggregate vesicles to H-aggregate tubes can be achieved by increasing the volume fraction of methanol in the mixtures. H-aggregate vesicles and tubes show two blue-shifted absorption bands and strong fluorescence, which result from the inclined arrangement of DiSC2(3) molecules. Furthermore, light-harvesting complexes are formed by adding dopamine (DA)-quinone (acceptor) in synthetic urine with H-aggregate vesicles or tubes. Our results show that H-aggregate tubes are more efficient than H-aggregate vesicles in transferring excited electrons to DA-quinone acceptors.